Sodium Cyanide → Ethyl 1-(cyanomethyl)cyclobutanecarboxylate

HRID 920734Notes

Reaction equation

HRID 920734 reaction equation
S(O[CH2:12][C:13]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:22]#[N:23].[Na+]>CS(C)=O.O>[C:22]([CH2:12][C:13]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15][CH2:16]1)#[N:23]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 118062693Ethyl 1-((tosyloxy)methyl)cyclobutanecarboxylate

Product 1

HCID 118061646Ethyl 1-(cyanomethyl)cyclobutanecarboxylateYield 41.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of Intermediate 220A (0.5 g, 1.601 mmol) in DMSO (2.5 mL) was added NaCN (0.196 g, 4.00 mmol) and the reaction mixture was stirred at 80° C. for 16 h. The reaction mixture was diluted with water and extracted with diethyl ether (3×30 mL) The combined organic layer was washed with water, dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 220B as a brown oil (0.110 g, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.19-4.01 (m, 2H), 3.01-2.97 (m, 2H), 2.45-2.32 (m, 2H), 2.08-1.83 (m, 4H), 1.25-1.18 (m, 3H).

Workup

  1. extractionextracted with diethyl ether (3×30 mL) The combined organic layer
  2. washwas washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d1bbd7eb60ba45408b2bce32189f483d
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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